Formed in 1691 in the Virginia Colony, Norfolk County had originally included essentially all the area which became the towns and later cities of Norfolk, Portsmouth, and South Norfolk. Its area was reduced after 1871 as these cities added territory through annexations. Becoming an independent city was a method for the former county to stabilize borders with neighbors, as cities could not annex territory from each other.

The relatively small city of South Norfolk had become an incorporated town within Norfolk County in 1919, and became an independent city in 1922. Its residents wanted to make a change to put their jurisdiction on a more equal footing in other aspects with the much larger cities of Norfolk and Portsmouth. In addition, by the late 1950s, although immune from annexation by the bigger cities, South Norfolk was close to losing all the county land adjoining it to the city of Norfolk in another annexation suit.

The consolidation that resulted in the city of Chesapeake was part of a wave of changes in the structure of local government in southeastern Virginia which took place between 1952 and 1975.

Until the late 1980s and early 1990s, much of Chesapeake was either suburban or rural, serving as a bedroom community of the adjacent cities of Norfolk and Virginia Beach with residents commuting to these locations. Beginning in the late 1980s and accelerating in the 1990s, however, Chesapeake saw significant growth, attracting numerous and significant industries and businesses of its own. This explosive growth quickly led to strains on the municipal infrastructure, ranging from intrusion of saltwater into the city’s water supply to congested roads and schools.

Chesapeake made national headlines in 2003 when, under a court-ordered change of venue, the community hosted the first trial of alleged Beltway sniperLee Boyd Malvo for shootings in 2002. A jury convicted him of murder but spared him a potential death sentence; it chose a sentence of “life in prison without parole” for the young man, who was 17 years old at the time of the crime spree. A jury in neighboring Virginia Beach convicted his older partner John Allen Muhammad and sentenced him to death for another of the attacks.